Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 8, Pages 3989-3993Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202013067
Keywords
alkene ligands; copper; cycloaddition; small-ring compounds; photocatalysis
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Funding
- NIH [GM095666, 1S10 OD020022-1]
- ACS-PRF [49817-ND1]
- NSF [CHE-1048642]
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The sole method available for the photocycloaddition of unconjugated aliphatic alkenes is the Cu-catalyzed Salomon-Kochi reaction. A new catalyst system with superior reactivity and photostability has been designed, offering significantly expanded substrate scope and highlighted through the preparation of the natural products sulcatine G and perforatol.
The sole method available for the photocycloaddition of unconjugated aliphatic alkenes is the Cu-catalyzed Salomon-Kochi reaction. The [Cu(OTf)](2).benzene catalyst that has been standard in this reaction for many decades, however, is air-sensitive, prone to photodecomposition, and poorly reactive towards sterically bulky alkene substrates. Using bench-stable precursors, an improved catalyst system with superior reactivity and photostability has been designed, and it offers significantly expanded substrate scope. The utility of this new catalyst for the preparation of sterically crowded cyclobutane structures is highlighted through the preparation of the cores of the natural products sulcatine G and perforatol.
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